DE2308798A1 - Vverfahren zur kernhydrierung von naryl-mono- und -polyamiden - Google Patents
Vverfahren zur kernhydrierung von naryl-mono- und -polyamidenInfo
- Publication number
- DE2308798A1 DE2308798A1 DE19732308798 DE2308798A DE2308798A1 DE 2308798 A1 DE2308798 A1 DE 2308798A1 DE 19732308798 DE19732308798 DE 19732308798 DE 2308798 A DE2308798 A DE 2308798A DE 2308798 A1 DE2308798 A1 DE 2308798A1
- Authority
- DE
- Germany
- Prior art keywords
- catalyst
- hydrogenation
- group
- aryl
- carbon atoms
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Withdrawn
Links
- 238000005984 hydrogenation reaction Methods 0.000 title claims description 75
- 238000000034 method Methods 0.000 title claims description 51
- 239000004952 Polyamide Substances 0.000 title claims description 40
- 229920002647 polyamide Polymers 0.000 title claims description 40
- 230000008569 process Effects 0.000 title claims description 9
- 239000003054 catalyst Substances 0.000 claims description 119
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 87
- 239000002253 acid Substances 0.000 claims description 39
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 claims description 36
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 239000010948 rhodium Substances 0.000 claims description 28
- 125000003118 aryl group Chemical group 0.000 claims description 26
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- OEXMNSOPAKOPEF-UHFFFAOYSA-N n-[4-[(4-acetamidophenyl)methyl]phenyl]acetamide Chemical compound C1=CC(NC(=O)C)=CC=C1CC1=CC=C(NC(C)=O)C=C1 OEXMNSOPAKOPEF-UHFFFAOYSA-N 0.000 claims description 23
- -1 phenylene, tolylene Chemical group 0.000 claims description 23
- 229910052703 rhodium Inorganic materials 0.000 claims description 23
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 14
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 14
- 239000002904 solvent Substances 0.000 claims description 14
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 13
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 claims description 13
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 11
- 239000011541 reaction mixture Substances 0.000 claims description 11
- 229910052707 ruthenium Inorganic materials 0.000 claims description 11
- 238000003756 stirring Methods 0.000 claims description 11
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims description 10
- 238000010306 acid treatment Methods 0.000 claims description 10
- 125000000217 alkyl group Chemical group 0.000 claims description 7
- 230000000694 effects Effects 0.000 claims description 7
- 229960001413 acetanilide Drugs 0.000 claims description 6
- 229910017052 cobalt Inorganic materials 0.000 claims description 6
- 239000010941 cobalt Substances 0.000 claims description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 6
- XAHUNQAOCGDSBW-UHFFFAOYSA-N n-(3-acetamido-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C(NC(C)=O)=C1 XAHUNQAOCGDSBW-UHFFFAOYSA-N 0.000 claims description 6
- GARRJFMMGMBXKL-UHFFFAOYSA-N n-[4-[(4-acetamidocyclohexyl)methyl]cyclohexyl]acetamide Chemical compound C1CC(NC(=O)C)CCC1CC1CCC(NC(C)=O)CC1 GARRJFMMGMBXKL-UHFFFAOYSA-N 0.000 claims description 6
- 229910052759 nickel Inorganic materials 0.000 claims description 6
- 229910052763 palladium Inorganic materials 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 5
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 239000000463 material Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 229910052741 iridium Inorganic materials 0.000 claims description 4
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052762 osmium Inorganic materials 0.000 claims description 4
- SYQBFIAQOQZEGI-UHFFFAOYSA-N osmium atom Chemical compound [Os] SYQBFIAQOQZEGI-UHFFFAOYSA-N 0.000 claims description 4
- 238000011065 in-situ storage Methods 0.000 claims description 3
- UQVKNKXDSWRQJE-UHFFFAOYSA-N n-(3-acetamidophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(NC(C)=O)=C1 UQVKNKXDSWRQJE-UHFFFAOYSA-N 0.000 claims description 3
- KVEDKKLZCJBVNP-UHFFFAOYSA-N n-(4-acetamidophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(NC(C)=O)C=C1 KVEDKKLZCJBVNP-UHFFFAOYSA-N 0.000 claims description 3
- ULUIRSHKJWANPP-UHFFFAOYSA-N n-(5-acetamidonaphthalen-1-yl)acetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC=CC2=C1NC(C)=O ULUIRSHKJWANPP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004957 naphthylene group Chemical group 0.000 claims description 3
- NAXDRCLBFGZQSR-UHFFFAOYSA-N n-(3-acetamido-2-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(NC(C)=O)=C1C NAXDRCLBFGZQSR-UHFFFAOYSA-N 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 239000012442 inert solvent Substances 0.000 claims 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims 1
- 125000005628 tolylene group Chemical group 0.000 claims 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
- 238000002474 experimental method Methods 0.000 description 27
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000006243 chemical reaction Methods 0.000 description 19
- 229910052757 nitrogen Inorganic materials 0.000 description 17
- 238000004458 analytical method Methods 0.000 description 13
- 238000010521 absorption reaction Methods 0.000 description 10
- 239000007795 chemical reaction product Substances 0.000 description 10
- 239000007789 gas Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 9
- 150000002431 hydrogen Chemical class 0.000 description 8
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 8
- 229920000768 polyamine Polymers 0.000 description 8
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 7
- 230000007062 hydrolysis Effects 0.000 description 7
- 238000006460 hydrolysis reaction Methods 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 125000001424 substituent group Chemical group 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- 230000004913 activation Effects 0.000 description 5
- 230000010933 acylation Effects 0.000 description 5
- 238000005917 acylation reaction Methods 0.000 description 5
- 235000019441 ethanol Nutrition 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 125000002723 alicyclic group Chemical group 0.000 description 4
- 238000005119 centrifugation Methods 0.000 description 4
- 230000007420 reactivation Effects 0.000 description 4
- MSXVEPNJUHWQHW-UHFFFAOYSA-N 2-methylbutan-2-ol Chemical compound CCC(C)(C)O MSXVEPNJUHWQHW-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 3
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000007522 mineralic acids Chemical class 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- UHANVDZCDNSILX-UHFFFAOYSA-N n-phenylbutanamide Chemical compound CCCC(=O)NC1=CC=CC=C1 UHANVDZCDNSILX-UHFFFAOYSA-N 0.000 description 3
- 230000009467 reduction Effects 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- HNRMPXKDFBEGFZ-UHFFFAOYSA-N 2,2-dimethylbutane Chemical compound CCC(C)(C)C HNRMPXKDFBEGFZ-UHFFFAOYSA-N 0.000 description 2
- BPTWDPQCIAXYNC-UHFFFAOYSA-N 2,3-diacetamidobenzoic acid Chemical compound CC(=O)NC1=CC=CC(C(O)=O)=C1NC(C)=O BPTWDPQCIAXYNC-UHFFFAOYSA-N 0.000 description 2
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical compound CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 2
- AFABGHUZZDYHJO-UHFFFAOYSA-N 2-Methylpentane Chemical compound CCCC(C)C AFABGHUZZDYHJO-UHFFFAOYSA-N 0.000 description 2
- YIWUKEYIRIRTPP-UHFFFAOYSA-N 2-ethylhexan-1-ol Chemical compound CCCCC(CC)CO YIWUKEYIRIRTPP-UHFFFAOYSA-N 0.000 description 2
- PFEOZHBOMNWTJB-UHFFFAOYSA-N 3-methylpentane Chemical compound CCC(C)CC PFEOZHBOMNWTJB-UHFFFAOYSA-N 0.000 description 2
- WCQSEJSRAJSUSS-UHFFFAOYSA-N 4-acetamido-3-methylbenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1C WCQSEJSRAJSUSS-UHFFFAOYSA-N 0.000 description 2
- QCXJEYYXVJIFCE-UHFFFAOYSA-N 4-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1 QCXJEYYXVJIFCE-UHFFFAOYSA-N 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- QSACCXVHEVWNMX-UHFFFAOYSA-N N-acetylanthranilic acid Chemical compound CC(=O)NC1=CC=CC=C1C(O)=O QSACCXVHEVWNMX-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 2
- 238000000921 elemental analysis Methods 0.000 description 2
- 125000004494 ethyl ester group Chemical group 0.000 description 2
- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 2
- 150000002430 hydrocarbons Chemical class 0.000 description 2
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- ZTHRQJQJODGZHV-UHFFFAOYSA-N n-phenylpropanamide Chemical compound CCC(=O)NC1=CC=CC=C1 ZTHRQJQJODGZHV-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- 150000007524 organic acids Chemical class 0.000 description 2
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 2
- KMUONIBRACKNSN-UHFFFAOYSA-N potassium dichromate Chemical compound [K+].[K+].[O-][Cr](=O)(=O)O[Cr]([O-])(=O)=O KMUONIBRACKNSN-UHFFFAOYSA-N 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- 230000035484 reaction time Effects 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- UJAOSPFULOFZRR-UHFFFAOYSA-N (4-acetamidophenyl) acetate Chemical compound CC(=O)NC1=CC=C(OC(C)=O)C=C1 UJAOSPFULOFZRR-UHFFFAOYSA-N 0.000 description 1
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GDXHBFHOEYVPED-UHFFFAOYSA-N 1-(2-butoxyethoxy)butane Chemical compound CCCCOCCOCCCC GDXHBFHOEYVPED-UHFFFAOYSA-N 0.000 description 1
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 1
- PZHIWRCQKBBTOW-UHFFFAOYSA-N 1-ethoxybutane Chemical compound CCCCOCC PZHIWRCQKBBTOW-UHFFFAOYSA-N 0.000 description 1
- BPIUIOXAFBGMNB-UHFFFAOYSA-N 1-hexoxyhexane Chemical compound CCCCCCOCCCCCC BPIUIOXAFBGMNB-UHFFFAOYSA-N 0.000 description 1
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 1
- AOPDRZXCEAKHHW-UHFFFAOYSA-N 1-pentoxypentane Chemical compound CCCCCOCCCCC AOPDRZXCEAKHHW-UHFFFAOYSA-N 0.000 description 1
- CZIHNRWJTSTCEX-UHFFFAOYSA-N 2 Acetylaminofluorene Chemical compound C1=CC=C2C3=CC=C(NC(=O)C)C=C3CC2=C1 CZIHNRWJTSTCEX-UHFFFAOYSA-N 0.000 description 1
- UZGYKGBZSGOYCM-UHFFFAOYSA-N 2,4-diacetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C(NC(C)=O)=C1 UZGYKGBZSGOYCM-UHFFFAOYSA-N 0.000 description 1
- IODDAJWYHNKAOV-UHFFFAOYSA-N 2,5-diacetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(NC(C)=O)C(C(O)=O)=C1 IODDAJWYHNKAOV-UHFFFAOYSA-N 0.000 description 1
- BOEMFEOUVXWWNZ-UHFFFAOYSA-N 2-(2-acetamidophenyl)acetic acid Chemical compound CC(=O)NC1=CC=CC=C1CC(O)=O BOEMFEOUVXWWNZ-UHFFFAOYSA-N 0.000 description 1
- LUSVQRVZKWYZSU-UHFFFAOYSA-N 2-acetamido-3-methylbenzoic acid Chemical compound CC(=O)NC1=C(C)C=CC=C1C(O)=O LUSVQRVZKWYZSU-UHFFFAOYSA-N 0.000 description 1
- XQQLTBPENCZOIE-UHFFFAOYSA-N 2-acetamido-5-methylbenzoic acid Chemical compound CC(=O)NC1=CC=C(C)C=C1C(O)=O XQQLTBPENCZOIE-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- WOYWLLHHWAMFCB-UHFFFAOYSA-N 2-ethylhexyl acetate Chemical compound CCCCC(CC)COC(C)=O WOYWLLHHWAMFCB-UHFFFAOYSA-N 0.000 description 1
- GXDHCNNESPLIKD-UHFFFAOYSA-N 2-methylhexane Chemical compound CCCCC(C)C GXDHCNNESPLIKD-UHFFFAOYSA-N 0.000 description 1
- GHTLCMPYQOFKCS-UHFFFAOYSA-N 3,4-diacetamidobenzoic acid Chemical compound CC(=O)NC1=CC=C(C(O)=O)C=C1NC(C)=O GHTLCMPYQOFKCS-UHFFFAOYSA-N 0.000 description 1
- FGHGVZVGAYQACH-UHFFFAOYSA-N 3-acetamido-4-methylbenzoic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=CC=C1C FGHGVZVGAYQACH-UHFFFAOYSA-N 0.000 description 1
- RGDPZMQZWZMONQ-UHFFFAOYSA-N 3-acetamidobenzoic acid Chemical compound CC(=O)NC1=CC=CC(C(O)=O)=C1 RGDPZMQZWZMONQ-UHFFFAOYSA-N 0.000 description 1
- ONSCGVISIRLDJQ-UHFFFAOYSA-N 3-acetamidophthalic acid Chemical compound CC(=O)NC1=CC=CC(C(O)=O)=C1C(O)=O ONSCGVISIRLDJQ-UHFFFAOYSA-N 0.000 description 1
- SVLDILRDQOVJED-UHFFFAOYSA-N 4-Acetylaminobiphenyl Chemical group C1=CC(NC(=O)C)=CC=C1C1=CC=CC=C1 SVLDILRDQOVJED-UHFFFAOYSA-N 0.000 description 1
- YICAMJWHIUMFDI-UHFFFAOYSA-N 4-acetamidotoluene Chemical compound CC(=O)NC1=CC=C(C)C=C1 YICAMJWHIUMFDI-UHFFFAOYSA-N 0.000 description 1
- CPIVYSAVIPTCCX-UHFFFAOYSA-N 4-methylpentan-2-yl acetate Chemical compound CC(C)CC(C)OC(C)=O CPIVYSAVIPTCCX-UHFFFAOYSA-N 0.000 description 1
- KQQYZSYKZQESPQ-UHFFFAOYSA-N 5-acetamidobenzene-1,3-dicarboxylic acid Chemical compound CC(=O)NC1=CC(C(O)=O)=CC(C(O)=O)=C1 KQQYZSYKZQESPQ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- VZHOBKXQZWSIMB-UHFFFAOYSA-N CC(C)C1C=CC(C)=CC1(NC(C)=O)O Chemical compound CC(C)C1C=CC(C)=CC1(NC(C)=O)O VZHOBKXQZWSIMB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 1
- AQZGPSLYZOOYQP-UHFFFAOYSA-N Diisoamyl ether Chemical compound CC(C)CCOCCC(C)C AQZGPSLYZOOYQP-UHFFFAOYSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical compound CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- NHTMVDHEPJAVLT-UHFFFAOYSA-N Isooctane Chemical compound CC(C)CC(C)(C)C NHTMVDHEPJAVLT-UHFFFAOYSA-N 0.000 description 1
- UYQKZKVNYKOXHG-UHFFFAOYSA-N Methyl n-acetylanthranilate Chemical compound COC(=O)C1=CC=CC=C1NC(C)=O UYQKZKVNYKOXHG-UHFFFAOYSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- GFXDUEWAGNGAMP-UHFFFAOYSA-N N-(1-acetamidonaphthalen-2-yl)acetamide Chemical compound C(C)(=O)NC1=C(C=CC2=CC=CC=C12)NC(C)=O GFXDUEWAGNGAMP-UHFFFAOYSA-N 0.000 description 1
- JCSIJMSQJUDFBY-UHFFFAOYSA-N N-(5-acetamido-1,2-dihydroacenaphthylen-4-yl)acetamide Chemical compound C(C)(=O)NC=1C=C2CCC=3C=CC=C(C=1NC(C)=O)C=32 JCSIJMSQJUDFBY-UHFFFAOYSA-N 0.000 description 1
- SNPZDXACCGIJNK-UHFFFAOYSA-N N-Acetyl-2,6-diethylaniline Chemical compound CCC1=CC=CC(CC)=C1NC(C)=O SNPZDXACCGIJNK-UHFFFAOYSA-N 0.000 description 1
- WRAGCBBWIYQMRF-UHFFFAOYSA-N N-Cyclohexylacetamide Chemical compound CC(=O)NC1CCCCC1 WRAGCBBWIYQMRF-UHFFFAOYSA-N 0.000 description 1
- ICGSBDQCZFDDRS-UHFFFAOYSA-N N-[4-[(4-acetamidophenyl)methyl]cyclohexyl]acetamide Chemical compound C(C)(=O)NC1CCC(CC1)CC1=CC=C(C=C1)NC(C)=O ICGSBDQCZFDDRS-UHFFFAOYSA-N 0.000 description 1
- WOYOJAPRKMBKEU-UHFFFAOYSA-N N1-(2,3-Dihydro-1H-inden-5-yl)acetamide Chemical compound CC(=O)NC1=CC=C2CCCC2=C1 WOYOJAPRKMBKEU-UHFFFAOYSA-N 0.000 description 1
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 206010035148 Plague Diseases 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 239000001089 [(2R)-oxolan-2-yl]methanol Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000004450 alkenylene group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical group C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 239000004760 aramid Substances 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000004984 aromatic diamines Chemical class 0.000 description 1
- 229920003235 aromatic polyamide Polymers 0.000 description 1
- 239000010425 asbestos Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- ZVSKZLHKADLHSD-UHFFFAOYSA-N benzanilide Chemical compound C=1C=CC=CC=1C(=O)NC1=CC=CC=C1 ZVSKZLHKADLHSD-UHFFFAOYSA-N 0.000 description 1
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 description 1
- 229940043232 butyl acetate Drugs 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 125000004181 carboxyalkyl group Chemical group 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000003245 coal Substances 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 125000000000 cycloalkoxy group Chemical group 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 description 1
- VDBXLXRWMYNMHL-UHFFFAOYSA-N decanediamide Chemical compound NC(=O)CCCCCCCCC(N)=O VDBXLXRWMYNMHL-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- NHLOBHNRBWKNIO-UHFFFAOYSA-N ethyl 4-acetamidobenzoate Chemical compound CCOC(=O)C1=CC=C(NC(C)=O)C=C1 NHLOBHNRBWKNIO-UHFFFAOYSA-N 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 125000000219 ethylidene group Chemical group [H]C(=[*])C([H])([H])[H] 0.000 description 1
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000000543 intermediate Substances 0.000 description 1
- GJRQTCIYDGXPES-UHFFFAOYSA-N iso-butyl acetate Natural products CC(C)COC(C)=O GJRQTCIYDGXPES-UHFFFAOYSA-N 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- FGKJLKRYENPLQH-UHFFFAOYSA-M isocaproate Chemical compound CC(C)CCC([O-])=O FGKJLKRYENPLQH-UHFFFAOYSA-M 0.000 description 1
- JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
- 229940011051 isopropyl acetate Drugs 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
- OQAGVSWESNCJJT-UHFFFAOYSA-N isovaleric acid methyl ester Natural products COC(=O)CC(C)C OQAGVSWESNCJJT-UHFFFAOYSA-N 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- QKWTXJSLAZKYGV-UHFFFAOYSA-N methyl 4-acetamidobenzoate Chemical compound COC(=O)C1=CC=C(NC(C)=O)C=C1 QKWTXJSLAZKYGV-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- RXTNIJMLAQNTEG-UHFFFAOYSA-N methylamyl acetate Natural products CCCCC(C)OC(C)=O RXTNIJMLAQNTEG-UHFFFAOYSA-N 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- RXRZTIATQMVXOK-UHFFFAOYSA-N n-(1,2-dihydroacenaphthylen-5-yl)acetamide Chemical compound C1CC2=CC=CC3=C2C1=CC=C3NC(=O)C RXRZTIATQMVXOK-UHFFFAOYSA-N 0.000 description 1
- QCZUDKNSUTYJAK-UHFFFAOYSA-N n-(2,4,5-triacetamidophenyl)acetamide Chemical compound CC(=O)NC1=CC(NC(C)=O)=C(NC(C)=O)C=C1NC(C)=O QCZUDKNSUTYJAK-UHFFFAOYSA-N 0.000 description 1
- LQWWZVZGPVVZOB-UHFFFAOYSA-N n-(2,4,6-trimethylphenyl)acetamide Chemical compound CC(=O)NC1=C(C)C=C(C)C=C1C LQWWZVZGPVVZOB-UHFFFAOYSA-N 0.000 description 1
- HOZRMSVNIKYCMB-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)acetamide Chemical compound COC1=CC=C(OC)C(NC(C)=O)=C1 HOZRMSVNIKYCMB-UHFFFAOYSA-N 0.000 description 1
- VMOQGOAWGLCADB-UHFFFAOYSA-N n-(2-acetamido-4,5-dimethylphenyl)acetamide Chemical compound CC(=O)NC1=CC(C)=C(C)C=C1NC(C)=O VMOQGOAWGLCADB-UHFFFAOYSA-N 0.000 description 1
- RLARNJBPODGLAZ-UHFFFAOYSA-N n-(2-acetamidophenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1NC(C)=O RLARNJBPODGLAZ-UHFFFAOYSA-N 0.000 description 1
- YSZGCNKBKQQPAH-UHFFFAOYSA-N n-(2-acetylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC=C1C(C)=O YSZGCNKBKQQPAH-UHFFFAOYSA-N 0.000 description 1
- SQRTWLGWCOJOTO-UHFFFAOYSA-N n-(2-ethoxyphenyl)acetamide Chemical compound CCOC1=CC=CC=C1NC(C)=O SQRTWLGWCOJOTO-UHFFFAOYSA-N 0.000 description 1
- ZXOVAGUQXNXKHF-UHFFFAOYSA-N n-(2-ethylphenyl)acetamide Chemical compound CCC1=CC=CC=C1NC(C)=O ZXOVAGUQXNXKHF-UHFFFAOYSA-N 0.000 description 1
- IXCZSZXIGHWLEJ-UHFFFAOYSA-N n-(2-phenylphenyl)acetamide Chemical group CC(=O)NC1=CC=CC=C1C1=CC=CC=C1 IXCZSZXIGHWLEJ-UHFFFAOYSA-N 0.000 description 1
- INRZVNSRCFDACA-UHFFFAOYSA-N n-(3,4-diacetamidophenyl)acetamide Chemical compound CC(=O)NC1=CC=C(NC(C)=O)C(NC(C)=O)=C1 INRZVNSRCFDACA-UHFFFAOYSA-N 0.000 description 1
- VFGJMNPXPQRBBN-UHFFFAOYSA-N n-(3,5-diacetamido-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC(NC(C)=O)=C(C)C(NC(C)=O)=C1 VFGJMNPXPQRBBN-UHFFFAOYSA-N 0.000 description 1
- KIMPOEOLEXUJEX-UHFFFAOYSA-N n-(3,5-diacetamidophenyl)acetamide Chemical compound CC(=O)NC1=CC(NC(C)=O)=CC(NC(C)=O)=C1 KIMPOEOLEXUJEX-UHFFFAOYSA-N 0.000 description 1
- OKOWOYJLYGCVSF-UHFFFAOYSA-N n-(3,5-dimethoxyphenyl)acetamide Chemical compound COC1=CC(NC(C)=O)=CC(OC)=C1 OKOWOYJLYGCVSF-UHFFFAOYSA-N 0.000 description 1
- KQJXHDWKWOKWGM-UHFFFAOYSA-N n-(3-acetamido-4-methoxyphenyl)acetamide Chemical compound COC1=CC=C(NC(C)=O)C=C1NC(C)=O KQJXHDWKWOKWGM-UHFFFAOYSA-N 0.000 description 1
- LSHZJVPFDGODCQ-UHFFFAOYSA-N n-(3-acetamidonaphthalen-2-yl)acetamide Chemical compound C1=CC=C2C=C(NC(C)=O)C(NC(=O)C)=CC2=C1 LSHZJVPFDGODCQ-UHFFFAOYSA-N 0.000 description 1
- SDLHRUDTCAGBLQ-UHFFFAOYSA-N n-(3-benzamidophenyl)benzamide Chemical compound C=1C=CC=CC=1C(=O)NC(C=1)=CC=CC=1NC(=O)C1=CC=CC=C1 SDLHRUDTCAGBLQ-UHFFFAOYSA-N 0.000 description 1
- OIEFZHJNURGFFI-UHFFFAOYSA-N n-(3-methoxyphenyl)acetamide Chemical compound COC1=CC=CC(NC(C)=O)=C1 OIEFZHJNURGFFI-UHFFFAOYSA-N 0.000 description 1
- ALMHSXDYCFOZQD-UHFFFAOYSA-N n-(3-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=CC(C)=C1 ALMHSXDYCFOZQD-UHFFFAOYSA-N 0.000 description 1
- ZYCWUKASEILJBB-UHFFFAOYSA-N n-(4-acetamido-3-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(NC(C)=O)C(C)=C1 ZYCWUKASEILJBB-UHFFFAOYSA-N 0.000 description 1
- HQQXWLXWAUYDAW-UHFFFAOYSA-N n-(4-propylphenyl)acetamide Chemical compound CCCC1=CC=C(NC(C)=O)C=C1 HQQXWLXWAUYDAW-UHFFFAOYSA-N 0.000 description 1
- NTZRFIYXMXPYCB-UHFFFAOYSA-N n-(5-acetamido-1,2,3,4,4a,5,6,7,8,8a-decahydronaphthalen-1-yl)acetamide Chemical compound CC(=O)NC1CCCC2C(NC(=O)C)CCCC21 NTZRFIYXMXPYCB-UHFFFAOYSA-N 0.000 description 1
- ZMJJQORILPSTPJ-UHFFFAOYSA-N n-(5-acetamido-9h-fluoren-2-yl)acetamide Chemical compound C1=CC(NC(C)=O)=C2C3=CC=C(NC(=O)C)C=C3CC2=C1 ZMJJQORILPSTPJ-UHFFFAOYSA-N 0.000 description 1
- XBZBRCVCSVLJJZ-UHFFFAOYSA-N n-(7-acetamido-9h-fluoren-2-yl)acetamide Chemical compound CC(=O)NC1=CC=C2C3=CC=C(NC(=O)C)C=C3CC2=C1 XBZBRCVCSVLJJZ-UHFFFAOYSA-N 0.000 description 1
- VVWRDFMDFFXMTP-UHFFFAOYSA-N n-(8-acetamidonaphthalen-1-yl)acetamide Chemical compound C1=CC(NC(C)=O)=C2C(NC(=O)C)=CC=CC2=C1 VVWRDFMDFFXMTP-UHFFFAOYSA-N 0.000 description 1
- PYGNVSDRIIPHQP-UHFFFAOYSA-N n-(9-oxofluoren-2-yl)acetamide Chemical compound C1=CC=C2C(=O)C3=CC(NC(=O)C)=CC=C3C2=C1 PYGNVSDRIIPHQP-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- CQISYTXUORWJSX-UHFFFAOYSA-N n-[4-(octadecanoylamino)phenyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=C(NC(=O)CCCCCCCCCCCCCCCCC)C=C1 CQISYTXUORWJSX-UHFFFAOYSA-N 0.000 description 1
- NIGRIMOLDFBQPY-UHFFFAOYSA-N n-[4-[(4-formamidophenyl)methyl]phenyl]formamide Chemical compound C1=CC(NC=O)=CC=C1CC1=CC=C(NC=O)C=C1 NIGRIMOLDFBQPY-UHFFFAOYSA-N 0.000 description 1
- ALQJVDUHVONSKS-UHFFFAOYSA-N n-[4-[[4-(octadecanoylamino)phenyl]methyl]phenyl]octadecanamide Chemical compound C1=CC(NC(=O)CCCCCCCCCCCCCCCCC)=CC=C1CC1=CC=C(NC(=O)CCCCCCCCCCCCCCCCC)C=C1 ALQJVDUHVONSKS-UHFFFAOYSA-N 0.000 description 1
- KASQAWDJNAPRLD-UHFFFAOYSA-N n-[5-(propanoylamino)naphthalen-1-yl]propanamide Chemical compound C1=CC=C2C(NC(=O)CC)=CC=CC2=C1NC(=O)CC KASQAWDJNAPRLD-UHFFFAOYSA-N 0.000 description 1
- QRIJEPHXWKXBDD-UHFFFAOYSA-N n-anthracen-1-ylacetamide Chemical compound C1=CC=C2C=C3C(NC(=O)C)=CC=CC3=CC2=C1 QRIJEPHXWKXBDD-UHFFFAOYSA-N 0.000 description 1
- NEXGLKJLQODWDW-UHFFFAOYSA-N n-anthracen-2-ylacetamide Chemical compound C1=CC=CC2=CC3=CC(NC(=O)C)=CC=C3C=C21 NEXGLKJLQODWDW-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DAGREVIJRSHSFZ-UHFFFAOYSA-N n-chrysen-6-ylacetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC3=C(C=CC=C4)C4=CC=C3C2=C1 DAGREVIJRSHSFZ-UHFFFAOYSA-N 0.000 description 1
- KERBAAIBDHEFDD-UHFFFAOYSA-N n-ethylformamide Chemical compound CCNC=O KERBAAIBDHEFDD-UHFFFAOYSA-N 0.000 description 1
- KEMFSGIRESMWFE-UHFFFAOYSA-N n-fluoranthen-3-ylacetamide Chemical compound C12=CC=CC=C2C2=CC=CC3=C2C1=CC=C3NC(=O)C KEMFSGIRESMWFE-UHFFFAOYSA-N 0.000 description 1
- OKQIEBVRUGLWOR-UHFFFAOYSA-N n-naphthalen-1-ylacetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC=CC2=C1 OKQIEBVRUGLWOR-UHFFFAOYSA-N 0.000 description 1
- DIEOESIZLAHURK-UHFFFAOYSA-N n-naphthalen-2-ylacetamide Chemical compound C1=CC=CC2=CC(NC(=O)C)=CC=C21 DIEOESIZLAHURK-UHFFFAOYSA-N 0.000 description 1
- WFBZMYPAVBCTCU-UHFFFAOYSA-N n-phenanthren-9-ylacetamide Chemical compound C1=CC=C2C(NC(=O)C)=CC3=CC=CC=C3C2=C1 WFBZMYPAVBCTCU-UHFFFAOYSA-N 0.000 description 1
- JBTCHCWUNMZNEO-UHFFFAOYSA-N n-phenylhexanamide Chemical compound CCCCCC(=O)NC1=CC=CC=C1 JBTCHCWUNMZNEO-UHFFFAOYSA-N 0.000 description 1
- ZOLJFBQEKSZVCB-UHFFFAOYSA-N n-phenyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NC1=CC=CC=C1 ZOLJFBQEKSZVCB-UHFFFAOYSA-N 0.000 description 1
- GJNGMQYHOZFQNX-UHFFFAOYSA-N n-pyren-1-ylacetamide Chemical compound C1=C2C(NC(=O)C)=CC=C(C=C3)C2=C2C3=CC=CC2=C1 GJNGMQYHOZFQNX-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- CPJSUEIXXCENMM-UHFFFAOYSA-N phenacetin Chemical compound CCOC1=CC=C(NC(C)=O)C=C1 CPJSUEIXXCENMM-UHFFFAOYSA-N 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 description 1
- 229940080818 propionamide Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000000171 quenching effect Effects 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000012066 reaction slurry Substances 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 229910052895 riebeckite Inorganic materials 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 238000001256 steam distillation Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/90—Regeneration or reactivation
- B01J23/96—Regeneration or reactivation of catalysts comprising metals, oxides or hydroxides of the noble metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/38—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals
- B01J23/40—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of noble metals of the platinum group metals
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyamides (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US228355A US3867443A (en) | 1972-02-22 | 1972-02-22 | Nuclear hydrogenation of n-aryl polyamides |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2308798A1 true DE2308798A1 (de) | 1973-08-30 |
Family
ID=22856850
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19732308798 Withdrawn DE2308798A1 (de) | 1972-02-22 | 1973-02-22 | Vverfahren zur kernhydrierung von naryl-mono- und -polyamiden |
Country Status (11)
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4069240A (en) * | 1975-09-04 | 1978-01-17 | Uniroyal, Inc. | Nuclear hydrogenation of n-aryl carbamates |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2447361A (en) * | 1945-12-20 | 1948-08-17 | Merck & Co Inc | dl-nu-cyclohexylacetylserine hexahydrobenzyl amide |
CH313261A (de) * | 1952-08-26 | 1956-03-31 | Ciba Geigy | Verfahren zur Herstellung einer neuen Hydrophenanthrencarbonsäure |
US2704281A (en) * | 1953-04-30 | 1955-03-15 | Universal Oil Prod Co | Purification of noble metal-metal oxide composite |
US3228975A (en) * | 1964-04-10 | 1966-01-11 | American Cyanamid Co | Akyl-substituted cyclohexyl guanidines and biguanides |
US3578395A (en) * | 1967-12-26 | 1971-05-11 | Chevron Res | Recovery of metals |
US3591635A (en) * | 1968-09-25 | 1971-07-06 | Upjohn Co | Catalytic hydrogenation process for preparing di(4 - aminocyclohexyl) methane |
-
0
- BE BE795668D patent/BE795668A/xx unknown
-
1972
- 1972-02-22 US US228355A patent/US3867443A/en not_active Expired - Lifetime
- 1972-07-18 CA CA147,368A patent/CA994363A/en not_active Expired
-
1973
- 1973-02-20 GB GB835173A patent/GB1416825A/en not_active Expired
- 1973-02-20 FR FR7305952A patent/FR2173064B1/fr not_active Expired
- 1973-02-21 IT IT67444/73A patent/IT977858B/it active
- 1973-02-21 AR AR246720A patent/AR195828A1/es active
- 1973-02-22 DE DE19732308798 patent/DE2308798A1/de not_active Withdrawn
- 1973-02-22 NL NL7302459A patent/NL7302459A/xx not_active Application Discontinuation
- 1973-02-22 BR BR731320A patent/BR7301320D0/pt unknown
- 1973-02-22 JP JP48021741A patent/JPS48103545A/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
FR2173064B1 (US20050192411A1-20050901-C00001.png) | 1975-10-31 |
BE795668A (fr) | 1973-08-20 |
IT977858B (it) | 1974-09-20 |
CA994363A (en) | 1976-08-03 |
BR7301320D0 (pt) | 1974-02-19 |
JPS48103545A (US20050192411A1-20050901-C00001.png) | 1973-12-25 |
AR195828A1 (es) | 1973-11-09 |
FR2173064A1 (US20050192411A1-20050901-C00001.png) | 1973-10-05 |
NL7302459A (US20050192411A1-20050901-C00001.png) | 1973-08-24 |
GB1416825A (en) | 1975-12-10 |
US3867443A (en) | 1975-02-18 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
DE1200821B (de) | Verfahren zur Hydrierung von carbonylgruppen-freien organischen Verbindungen | |
DE1948566B2 (de) | Verfahren zur herstellung von di(4-aminocyclohexyl)-methan durch katalytische hydrierung von di-(4-aminophenyl)-methan | |
DE69219059T2 (de) | Verfahren zur Herstellung von Bisaminomethylcyclohexane | |
DE2164341A1 (de) | Herstellung von Hexamethylendiamin | |
DE2118369A1 (de) | Selektive Hydrierung von Nitroaromaten | |
EP0238961B1 (de) | Verfahren zur Herstellung von Hydroxyaminen | |
DE2502894C3 (de) | Ruthenium-Trägerkatalysator | |
DE1518345C3 (de) | Verfahren zur Herstellung von Trimethylhexamethylendiaminen | |
WO1996020165A1 (de) | Verfahren zur herstellung von aliphatischen alpha, omega-aminonitrilen | |
DE2455887C2 (de) | Verfahren zur Herstellung von chlorierten Phenylhydroxylaminen | |
DE2551055A1 (de) | Verfahren zur herstellung von 1,3- oder 1,4-bis-(aminomethyl)-cyclohexan | |
EP0322760B2 (de) | Verfahren zur Herstellung von Kobaltkatalysatoren | |
DE2308798A1 (de) | Vverfahren zur kernhydrierung von naryl-mono- und -polyamiden | |
EP0960093A1 (de) | Verfahren zur hydrierung von verbindungen aus der gruppe der imine oder enamine | |
DE2459547C2 (de) | Verfahren zur Herstellung von Hexamethylenimin | |
DE915568C (de) | Verfahren zur Herstellung von siebengliedrigen Heterocyclen von der Art der Caprolactame und der Hexamethylenimine und von offenkettigen Stickstoffverbindungen | |
DE3003731A1 (de) | Verfahren zur hydrierung von aromatischen bis-methylaminen | |
DE2236777C2 (de) | Verfahren zur Herstellung von Diaminodiphenyläthern | |
DE2609209C2 (de) | Verfahren zur Herstellung von 2-Pyrrolidon | |
DE2024858A1 (US20050192411A1-20050901-C00001.png) | ||
EP0322761B1 (de) | Verfahren zur Herstellung von Dialkylaminoethylaminen | |
DE2014837A1 (de) | Verfahren zur Herstellung von Piperidin | |
EP0010179A1 (de) | Verfahren zur Herstellung von 2.2-Dialkyl-pentan-1.5-diaminen und die Verbindungen N-(4-Cyano-2.2-diethyl-butyl)-4-cyano-2.2-diethyl-butyliden-imin und N-(4-Cyano-2-n-butyl-2-ethyl-butyl)-4-cyano-2-n-butyl-2-ethyl-butyliden-imin | |
DE2655794A1 (de) | Verfahren zur herstellung von aethylencyanhydrin | |
DE1468779A1 (de) | Verfahren zur Herstellung von Dicyclohexylaminen aus Dicyclohexanolen |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
OD | Request for examination | ||
8128 | New person/name/address of the agent |
Representative=s name: BERENDT, T., DIPL.-CHEM. DR., PAT.-ANW., 8000 MUEN |
|
8130 | Withdrawal |